8 of the Most Charming Small Towns to Visit in Chesapeake Bay
The Chesapeake Bay estuary stands alone in its category when it comes to its history, vastness, and beauty. The bay and its surrounding areas attract visitors from across the United States and the world, all looking to get a taste of this unique maritime way of life. Both Maryland’s and Virginia’s east coasts lie against the Chesapeake waters and are home to endless charming small towns that epitomize the traditional, yet laid back, coastal ways of living. If you are looking for a salty and fresh-aired escape from reality, look no further than the Chesapeake Bay!
Cambridge, Maryland
Rich with maritime heritage and east-coastal charm, the town of Cambridge, Maryland, is a quintessential stop during any visit to the Chesapeake Bay. While being a friendly, small, and tight-knit community, visitors to Cambridge still don’t have to miss out on what is also a world-class travel destination. The town is able to be enjoyed either on foot or by boat, and boasts countless popular attractions for its visitors. Take in the expansive Blackwater National Wildlife Refuge, an impressive 20,000 acres of marshland and forest with an incredible amount of animal and plant diversity. Additionally, visit the Richardson Maritime Museum or the Visitor Center at Sailwinds Park. Historically, Cambridge is also home to an essential figure of American social activism - Harriet Tubman. The Harriet Tubman Underground Railroad Visitor Center and Harriet Tubman Underground Railroad Scenic Byway are both sites that pay homage to this woman’s extraordinary life and legacy.
It would also be a mistake to discuss the town of Cambridge and not mention its mouth-watering dining scene. Immerse yourself here in what the bay has to offer, with incredibly fresh local seafood and countless traditional maritime dishes. In May, sit back with a beer from RAR Brewing and enjoy The Cambridge Classic - the country’s longest-running annual powerboat race.
Chesapeake City, Maryland
Listed on the Maryland as well as National Historic Register, Chesapeake City is a town you won’t want to miss out on. Spend hours exploring and getting lost in the beloved historic district - with picturesque local boutiques, restaurants, and antique stores all running along incredibly quaint and visually charming streets. Visitors can also choose to take in the town from an alternative, and arguably better, point of view by hopping on a Chesapeake City Water Tour Boat. Enjoy striking and original views of Chesapeake City and, notably, the Turkey Point Lighthouse, which can only be seen from the water.
Pay a visit to the C&D Canal Museum, the Ben Cardin Recreational Trail, the gorgeous Chesapeake Wine Trail, or the historic Mount Harmon Plantation. Then, after a long day of sightseeing and enjoying all that Chesapeake City has to offer, relax and unwind in one of several lovely Inns or Bed and Breakfasts. The Ship Watch Inn, Inn at the Canal, or The Blue Max Inn are all excellent and very highly rated options.
Chestertown, Maryland
Chestertown, Maryland, is known as a historical College Town - home to Washington College. Established in 1782, the college was the first to be chartered in the sovereign United States of America. It is not only a significant site but also a beautiful one to visit on any trip through Chestertown. Next to the college, visitors can stroll along cobblestone streets lined with restored 18th-century row houses - all found along the shores of the Chester River. Pause your explorations and endeavors for a croissant break at the beloved Evergrain Bread Company - known to have the best croissants to be found on this side of the ocean. Skeptical? You’ll have to pay a visit to find out for yourself!
Chestertown also has a thriving cultural scene, which can be found in its Arts and Entertainment District, which is located within the well-connected downtown area. There are year-round events and festivals, such as the Chestertown Tea Party Festival held over Memorial Day Weekend or the ‘Music in the Park’ annual Summer Concert Series. Lastly, enjoy the nearly year-round Chestertown Farmers and Artisans Market - an excellent way to orient yourself to the incredible east-coast local food and cultural scene.
Saint Micheals, Maryland
The historically rich Saint Micheals, Maryland, would truly be a quintessential location for the ultimate eastern shore getaway. Don’t let the small size of the town fool you, what it may ‘lack’ in size it makes up for in natural beauty, charm, and excitement. Saint Micheals truly comes alive in the summer, as this is the time of year when everything the town has to offer shines. The locals here are very friendly and welcoming, and all in all, Saint Micheals ends up being nothing short of refreshing, relaxing, and rejuvenating for locals and visitors alike. Pay a visit to either the St. Michaels Museum or the Chesapeake Bay Maritime Museum, or decide to truly make the most of your visit to the eastern shore and head out on the water. The organization Sail Selina II is able to offer visitors many fun and flexible ways to enjoy this element of Saint Micheals.
There is a bustling, walkable downtown area studded with historical Victorian buildings - now all home to modern and locally run shops and boutiques. This area is made for meandering and window shopping. Saint Micheals is also famous for its Maryland crabs and offers countless options for both traditional and modern food and drink.
Cape Charles, Virginia
A small and charming seaside town, Cape Charles, Virginia, is able to offer events and activities for every kind of visit. Either relax on the Cape Charles Town Beach or explore the surrounding waters via kayak. The largest state park on Cape Charles, Kiptopeke State Park, also provides access to gorgeous beaches on which to spend the day. Visitors can also book a fishing charter and experience an east coast catch on the waters of the Chesapeake Bay.
Alternatively, take a stroll through the vibrant historic district, with a large variety of charming Victorian and Colonial-era homes lining the streets. Wander through never-ending local shops and boutiques, where you can find all sorts of unique souvenirs and trinkets to remember your trip by. If you take a peek at the town’s bustling events calendar, it will also become clear that there is truly never a dull moment here in Cape Charles. There are countless fun and diverse community events held regularly for locals and visitors alike! We are talking about Community Spaghetti Dinner Nights, Women’s Wellness Weekends, regularly held storytimes for children, and so much more. From hiking, cycling, or bird watching to restorative beach yoga and coastal spas, there truly is something for everyone in Cape Charles.
Irvington, Virginia
Although the town of Irvington, Virginia, may be small, it offers countless cultural, natural, and commercial amenities that make it more than worthwhile to visit. During your stay here, enjoy a true Chesapeake Bay dining experience and savor the bay’s famous blue crabs or Rappahannock River Oysters next to award-winning local wines. Stop by the open-air Irvington farmers market, a regular event that truly captures the friendliness, hospitality, and community spirit that the Irvington locals have. Enjoy fresh local produce and flowers, baked goods, handcrafted gifts, and so much more - all alongside live music and incredible food. Irvington is also known to be a bird lover's paradise. If this calls your name, don’t deprive yourself of some incredible bird-watching along Carter’s Creek.
Additionally, pay a visit to the Steamboat Era Museum and learn more about a very significant time in Virginia and the Chesapeake Bay’s history through restored historical artifacts and interactive exhibits. Enjoy a bustling downtown area in Irvington, with countless options for dining and shopping, as well as galleries and antique stores. After days of exploring and probably eating, enjoy a rejuvenating stay at the historic Tide Inn, the primary place to spend your nights of sleep in Irvington. Nestled in an idyllic location along Carter’s Creek and nearby Chesapeake Bay, the Inn provides the ideal getaway for families, romantics, or adventurers alike.
Urbanna, Virginia
A laid-back colonial port town that claims to have more boats than people, Urbanna, Virginia, is the place to be if you are looking to unwind. Urbanna’s main claim to fame would absolutely be the iconic Oyster Festival held annually in November. The town typically only has a small population of people residing there year-round; however, when this autumn Oyster Festival rolls around, it is known to attract over 75,000 visitors who come exclusively for the iconic event.
In its origins, the town actually operated primarily as a tobacco port. Now, its friendly and tight-knit community hosts several unique and diverse local events, such as the free-to-all Urbanna Chili Cook-Off, its Farmers Market held on Saturdays, a wine and oyster stroll with live music, and even a Holiday Fashion Show with Champagne Brunch. Additionally, enjoy a ‘Second Saturday,’ a local Urbanna event held on the second Saturday of each month from May to September. Experience one-of-a-kind festivities here, complete with music, entertainment, crafts, and delicious food.
Rock Hall, Maryland
Located at the top of Chesapeake Bay, this quaint waterman’s town truly has it all. Visit Rock Hall’s Waterman’s Museum to experience a taste of traditional fishing, crabbing, and oystering in the Chesapeake Bay - or stop by the Rock Hall Museum to learn about the early days and evolution of Chesapeake living. Visitors can also experience the beauty of the bay through Shardana Sailing Charters. Head out onto the water and take in the area the way it was meant to - by boat. Throughout the excursion, learn more about the Chesapeake’s history, ecosystems, and the people who built it into what we know it today. Alternatively, you can choose to take matters into your own hands and take sailing lessons at the Delmarva Sailing School, affiliated with the American Sailing Association. Settled right on the Chesapeake Bay, take on a new adventure and savor the fresh bay air in a new way.
Besides boating and sailing, there are also many other ways to get to the beautiful Rock Hall. For example, the incredible Eastern Neck National Wildlife Refuge is a natural attraction that is not to be missed. Enjoy diverse ways of savoring this stunning area through activities such as birding, hiking, and kayaking.
Whether exploring the Chesapeake waters, experiencing the east-coast maritime dining culture, or strolling through culturally significant landmarks and areas, these towns nestled in the Chesapeake Bay truly have something for everyone. If you’re looking to get away from it all, whether with your family, friends, or partners, the Bay is truly able to accommodate and enhance every kind of trip. The salty, fresh bay air and social, friendly communities will have you and your loved ones coming back in no time looking for more. Prepare for a memorable, joyful, and relaxing time as you savor life in the charming Chesapeake Bay way.
